Azo dyes and process for their application



Patented Jan. 17 1939 g UNITED STATES PATENT OFFICE AZO DYES AND PROCESSFOR THEIR APPLICATION Swanic S. Rossander, Wilmington, Del., minor to E.I. du Pont dcyNemours & Company, Wil mlngton, DeL, a. corporation ofDelaware No Drawing. Application July 3, 1937,

1 Serial No. 151,964

6 Claims. (CL 8-46) This invention relates to new polyazo dyestuilslulose a dyestuil represented by the formula: for the coloring ofcellulose by development on Y l-N=N- -(N(aminoeroyD-emino-naphthol-sullonio acid)" the fiber. Demand has arisen inthe. trade for orange, red, brown, and scarlet dyes which imapartdesirable shades to cellulose, within which term is included tho e hi compounds Yaryl-N=N(N(amlno aroyD-emino-naphthol-sulionic acid) lmownas cellulose as well as those which in i h Y i e of a up c i t of arecalled regenerated cellulose, but the dyehalo en, hy 7 xy, and 71 is ofI stufl's of the prior art of satisfactory shade $111818 n ene 0inaphthalene nu m are generally unsatisfactory. in fastness to wash-These colors applied by impregnating cellum lose with a compoundrepresented by the formula:

dyes of the indicated colors which dye cellulose with pleasing effects,which are of excellent fast- -NZ-pz-(N(wim-amyD-amlno-naphtbol-sulionlcacid) 15 ness to washing. and which possess all the other f an aqueousbath, dlazotmng the compound attributes, such as substantivity anddurability, on the cellulose and coupling n which are ne ss for aSatisfactory commer- In-the following table are illustrations of the0181 Product invention. In this table PALB means para-amino- The objectsof the invention are accombenzoyl, MAB means meta-amino-benzoyl, and 20plished, generally speaking, by applying to celthe arrows. meandiazotized and coupled to.v

Ex. Diazo component Coupling component 535x 22 25 l l-(PAB amlno)2chlor-4-smino-benzene "(PAB I-ocid), Beta mphthol Rod. 2 dn Il,'phenyl-8-methyl-6-pyruolone- Orange. 80 3 -----do Accto acetanilideDo.

4 do H. 5 l-(PAB amino) 2-ch1or-4'smino-benzcno "'(MAB J-ecid); Betanaphthol Red. 6 l-(PAB amino) ZB-dimethoxy-Qamino- (PAD 1-0011!) Brown.1 is amino) 2'5-d1methoxy-4-emino-benzene (MAB I- ..-.-do.... Do. 35

a 8 1-2563 amino) 2-fi-dimethox y-bamlno-benzom '(PAB I- in I Do.

9 1-9358 amino) 2-6-dimethoxy-4-smlno-bcnmcne ,"(lll3 I- ...-do Do. a;10 14 amino) Z-methoxy-IS-methylMmIno-DenzenQ QAB i1 l-g ig igfmino)2methoxy-6-mcthyl-4-emino- .'(MAB I. 12 l-(PAB amino)4-emino-benzene-2-sulionic aold ,"(PAB Lucid) 7 l3 l-(PAB amino)5-amlno-benzene-2-sullonloaold :(l-'ABLucid) 45 14 l-(PAB amino)2-methoxy-4-amlno-benzenc ,"(PAB Lucid.-- I 15 l-(PAB amino)2-methoxy-4-amino-benzeno :(MAB Lucid-.. I 16 l-(PAB amino)z-mctliozy-t-emino-benzcne (PAB J-ecid) 11 l-(PAB ammo) 2methoxy-5-amino-benzene "(MAB I-ecidl- 1s l-(PAB amino) l-ammc-aahzhcienewhn J-acidh 19 l-(PAB amino) 4-amlno-naphthnlene ,'(MAB I-ccid20 l-(PAB amino) 4-amino-benzene-2-sulionic acid "(MAB I- acid):- 5G

21 'l-glzfill amino) ll-amino-bcnzone-t -sulionlc acid :(MAB 1- do Do.

I- 22 l-(PAB amino) z-iimino-naphthalene (PAB Iaoid do I Red. 23 l-(PABamino) 2-amino-naphthalene ."(MAB I-eci do Do.

Five parts of cotton piece goods are d-yed in the usual manner, known tothose-skilled in the art, with two hundredths parts of 1- (PAB amino)2-chlor-4-amino-benzene (para-amino-benzoyl-J-acid) 2.

The dyed fabric is rinsed in cold water and put in 200 parts of water at20 C. Add three tenths parts of sodium nitrite and four tenths part ofsulfuric acid. Stir 15 minutes. Rinse with cold in which E is a nucleusof a component from the group consisting of beta-naphthol,acetoacetanilide, meta-tolylene-diamine, and l-phenyl-3-methyl-5-pyrazolone, aryl is a component having a single benzene ornaphthalene nucleus, and Y is one of the group consisting of hydrogen,halogen, alkyl, and alkoxy.

As many apparently widely difierent embodiments of this invention may bemade without departing from the spirit and scope thereof, it is to beunderstood that I do not limit myself to the specific embodimentsthereof except as defined in the appended claims.

I claim:

1. A compound represented by the formula:

Y arylN=N(N(amino aroyD-amino-naphthol-sull'onic acid)-N=N-beta-naphtholI v Yaryl-N=N'(N(amino aroyl)-amino-naphthol-sulionicacid)-N=N-beta-nephthol water. Dissolve one-tenth part of beta naphtholin 200 parts Water and one twentieth part of caustic soda. Stir thesolution rapidly while adding the above rinsed piece goods. Stir for 15minutes. Rinse in cold water and dry. The dyein which Y is one or moreof a group consisting of halogen, hydrogen, alkyl, alkoxy, and sulfonicacid, and aryl is of single benzene or naphthalene nucleus.

2. A compound represented by the formula:

ing is a red shade. The probable formula of the dye on the fiber is:

=N-O-CONH on N=NOC ONEmS oBNa The same method is applicable to the otherdyes of this invention.

The new dyes are of outstanding fastness to washing when produced oncellulose by development. The compounds are generally represented by theformula:

in which Y is one or more of a group consisting of halogen, hydrogen,alkyl, alkoxy, and sulfonic C1 NaOaS beta-naphthol-N=,N

OONH SOaNa SOaNa beta-naphthol-N=N CONH OaNa 3. A compound representedby the formula:

N=N-beta-naphthol 01 more NHCO H 4. A compound represented by theformula:

SOaNa H ene-dlamlne, and l-phenyl-B-melzhyl-fi-pyrazo- 6. The proceqawhich comprises applylnkto celin which Y is one or more of the groupconslstlulose from an aqueous bath a compound repreing or hydrogen,albl, sulfonlc acid, halogen, and sented by the formula: v alkoxy,dlazotlzlng it :n the cellulose, and cou- Y ]...N=N. W 1 qmln m anon!add pllng it to 8, componen from the group consisting m (mm M mp orbetanaphthol, aoetoacet-anlllde, meta-tolyl- 5 5:0 lone.

